Amino acid promoted CuI-catalyzed C-N bond formation between aryl halides and amines or N-containing heterocycles

Journal of Organic Chemistry

Volumn 70, Issue 13, 2005, Pages 5164-5173

  Zhang, Hui ^a   Cai, Qian ^b   Ma, Dawei ^b  

^a FUDAN UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AMINO ACIDS; BROMINE COMPOUNDS; CARBON; CATALYSIS; CHEMICAL BONDS; ELECTRONS; NITROGEN;

ARYL IODIDES; IMIDAZOLE; N-METHYLGLYCINE; PYRAZOLE;

COPPER COMPOUNDS;

AMINO ACID; BROMIDE; CARBAZOLE DERIVATIVE; COPPER DERIVATIVE; HALIDE; IMIDAZOLE; INDOLE DERIVATIVE; IODINE DERIVATIVE; PYRAZOLE; PYRROLE; SARCOSINE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION;

AMINES; AMINO ACIDS; BENZENE DERIVATIVES; CATALYSIS; COPPER; GLYCINE; HALOGENS; INDICATORS AND REAGENTS; IODIDES; MOLECULAR STRUCTURE; PROLINE; TEMPERATURE;

EID: 20844435969     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0504464     Document Type: Article

References (57)

1. (a) Belfield, A.; Brown, G. R.; Foubister, A. J. Tetrahedron 1999, 55, 11399.
2. (b) Hong, Y.; Senanayake, C. H.; Xiang, T.; Vandenbossche, C. P.; Tanoury, G. J.; Bakale, R. P.; Wald, S. A. Tetrahedron Lett. 1998, 39, 3121.
3. (c) Goodbrand, H. B.; Hu, N. X. J. Org. Chem. 1999, 64, 670.
4. (d) O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435.
5. (a) Craig, P. N. In Comprehensive Medicinal Chemistry; Drayton, C. J., Ed.; Pergamon Press: New York, 1991; Vol. 8.
6. (b) Kundu, N. G.; Mahanty, J. S.; Chowdhurry, C.; Dasgupta, S. K.; Das, B.; Spears, C. P.; Balzarini, J.; De Clercq, E. Eur. J. Med. Chem. 1999, 34, 389.
7. (a) McClenaghan, N. D.; Passalacqua, R.; Loiseau, F.; Campagna, S.; Verheyde, B.; Hameurlaine, A.; Dehaen, W. J. Am. Chem. Soc. 2003, 125, 5356.
8. (b) Paredes, E.; Kneeteman, M.; Gonzalez-Sierra, M.; Mancini, P. M. E. Tetrahedron Lett. 2003, 44, 2943.
9. (c) Jian H.; Tour, J. M. J. Org. Chem. 2003, 68, 5091.
10. (d) Finn, J.; Mattia, K.; Morytko, M.; Ram, S.; Yang, Y.; Wu, X.; Mak, E.; Gallant, P.; Keith, D. Bioorg. Med. Chem. Lett. 2003, 13, 2231.
11. (e) Wang, X.; Tan, J.; Zhang, L. Org. Lett. 2000, 2, 3107.
12. (f) Smith, W. J.; Sawyer, J. S. Tetrahedron Lett. 1996, 37, 299 and references therein.
13. (a) Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382.
14. For reviews, see: (b) Lindley, J. Tetrahedron 1984, 40, 1433.
15. (c) Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359.
16. For reviews, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
17. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
18. (c) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
19. For reviews, see: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 15, 2428.
20. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
21. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337.
22. For other related studies, see: (d) Okano, K.; Tokuyama, H.; Fukuyama, T. Org. Lett. 2003, 5, 4987.
23. (e) Han, C.; Shen, R.; Su, S.; Porco, J. A., Jr. Org. Lett. 2004, 6, 27.
24. (f) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
25. (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727.
26. (b) Antilla, J. C.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 11684.
27. (c) Antilla, J. C.; Baskin, J. M.; Barder, T. E.; Bchwald, S. L. J. Org. Chem. 2004, 69, 5578.
28. (a) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
29. (b) Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793.
30. (a) Gujadhur, R. K.; Bates, C. G.; Venkataraman, D. Org. Lett. 2001, 3, 4315.
31. (b) van Allen, D.; Venkataraman, D. J. Org. Chem. 2003, 68, 4590.
32. (a) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Eur. J. Org. Chem. 2004, 695.
33. (b) Cristau, H.-J.; Cellier, P. P.; Spindler, J.-F.; Taillefer, M. Chem.-Eur. J. 2004, 10, 5607.
34. Zhang, S.; Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1997, 62, 2312.
35. (a) Ma, D.; Zhang, Y.; Yao, J.; Wu, S.; Tao, F. J. Am. Chem. Soc. 1998, 120, 12459.
36. (b) Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583.
37. (c) Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
38. (d) Ma, D.; Cai, Q. Org. Lett. 2003, 5, 3799.
39. (e) Ma, D.; Cai, Q. Synlett 2004, 1, 128.
40. (f) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809.
41. (g) Zhu, W.; Ma, D. Chem. Commun. 2004, 888.
42. (h) Ma, D.; Liu, F. Chem. Commun. 2004, 1934.
43. (i) Cai, Q.; Zhu, W.; Zhang, H.; Zhang, Y.; Ma, D. Synthesis 2005, 496.
44. For related work, see: (j) Deng, W.; Wang, Y.; Zou, W.; Liu, L.; Guo, Q. Tetrahedron Lett. 2004, 45, 2311.
45. (k) Deng, W.; Zou, Y.; Wang, Y. F.; Liu, F.; Guo, Q. X. Synlett 2004, 1254.
46. (a) Ji, J.; Li, T.; Bunnelle, W. H. Org. Lett. 2003, 5, 4611.
47. (b) Arterburn, J. B.; Pannala, M.; Gonzalez, A. M. Tetrahedron Lett. 2001, 42, 1425.
48. (c) Yin, J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M. Org. Lett. 2002, 4, 3481.
49. (d) Jonckers, T. H. M.; Maes, B. U. W.; Lemiere, G. L. F.; Dommisse, R. Tetrahedron 2001, 57, 7027.
50. Gujadhur, R. K.; Venkataraman, D.; Kintigh, J. T. Tetrahedron Lett. 2001, 42, 4791.
51. Cohen, T.; Wood, J.; Dietz, A. G., Jr. Tetrahedron Lett. 1974, 15, 3555.
52. Paine, A. J. J. Am. Chem. Soc. 1987, 109, 1496.
53. Greenstein, J, P.; Winitz, M. Chemistry of the Amino Acids; Wiley: New York, 1961; Vol. 3.
54. Aalten, H. L.; Van Koten, G.; Grove, D. M.; Kuilman, T.; Piekstra, O. G.; Hulshof, L. A.; Sheldon, R. A. Tetrahedron 1989, 45, 5565.
55. For emerging applications of the present N-aromation methodology, see: (a) Fletcher, S. P.; Clive, D. L. J.; Peng, J.; Wingert, D. A. Org. Lett. 2005, 7, 23.
56. (b) Jean, L.; Rouden, J.; Maddalauno, J.; Lasne, M.-C. J. Org. Chem. 2004, 69, 8893.
57. (c) Cuny, G.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2004, 126, 14475.